Articles

I have written every day for the past 10 years. If you like to read, I've got your back - and I promise to challenge your thinking

5 Ways to Master The Art (And Magic) Of Deep Coaching

Deep Coaching is an art, not a science. And its impact is magical.

Coaching is my life blood. And I love it.

But it wasn’t always that way.

My sweet spot is coaching talented high performers and leaders who have transitioned into coaching or consulting.

You see coaching is a natural leadership skill. All great leaders throughout history have been natural coaches. We just didn’t have a buzzword to describe it. We used to call it leadership!

There’s nothing more exciting than coaching someone with a track record of success.

Because, so often, it’s their very success that holding them back from their next big accomplishment. And they can’t see it…

And there’s nothing more exciting than coaching a leader who is on a mission bigger than anyone around them.

Because, after dreaming so big – counterintuitively – my job is to slow them down to their tiniest possible next step…

And there’s nothing more exciting than coaching a highly talented leader or an elite top performer.

Because I’m able to see the things they cannot see. And I’m willing to say what no one else will dare to say…

I used to think that the greatest challenge of Deep Coaching is that its Art and its Magic can’t be systematized. They can’t be ordered. They can’t be cataloged.

So, for many years, when coaches asked me to teach them how I coach, I resisted. A lot!

I loved to model and demonstrate the power of Deep Coaching (check out my YouTube playlist). But I never wanted to create a training around how to coach.

You see, Deep Coaching is so personal to the coach and to the client and to the situation that I was clear it couldn’t be codified.

But coaches didn’t stop asking me…

And then, one day I began reading Harry Potter to my little boys… (All three of us absolutely love the stories). And I began to realize that Magic can be taught!

And then I remembered that a few years ago I’d spent 4 months on a magic course at The Magic Castle, in Hollywood.

It’s a private members club for magicians – and the headquarters of the Academy of Magical Arts – one of the most unusual private clubs in the world. The entrance, in the lobby, is through a bookcase, which only opens to let you in when you say the correct magical password!

I was literally trained to do Magic.

And so I stopped. And I reflected. And I reflected some more.

And I spent the past two years peeling apart the layers of Deep Coaching.

Would you like to take a look at the 5 critical elements that allow you to coach the most talented high performers and leaders?

If you love to read, I’ve broken down the 5 elements below…  

And if you would rather see and hear me break them down, this is the first in a series of two videos I recorded for the World Business Executive Coach Summit on Deep Coaching:


  • Element #1: DEEP LISTENING
  • Element #2: ELICITING
  • Element #3: 10X
  • Element #4: LEADERSHIP
  • Element #5: STRATEGY

Element #1: DEEP LISTENING

This is the heart of Deep Coaching…  

  • It’s about PRESENCE – a willingness to be so present you can even sense a shift in your clients’ breathing.
  • It’s about SILENCE – one of the most powerful coaching tools in your toolkit.
  • It’s about SAFETY – an ability to create enough trust that you can get to the heart of what your clients really need.
  • It’s about CURIOSITY – with a focus on ‘interested’ questions (“Tell me more about that…”) vs ‘interesting’ questions (“Here’s what I think … How about you?”)
  • It’s about PROVOCATION – a willingness to use provocative and ‘obvious’ questions, to listen for what’s not said and to listen for the question behind the question.

Element #2: ELICITING

To elicit means to evoke or draw out. In this case, it’s 5 main things…   

  • THEIR DREAMS & THEIR FEARS – drawing out their secret desires and their deepest fears.
  • THEIR GIFTS – drawing out what they do exceptionally well, as well as their hidden gifts and also the dark side of their gifts.
  • THEIR THINKING – getting curious about how they think (beyond what they think) but also where their motivation and their energy come from.
  • THEIR CONTEXT – listening to the content of their stories but then draw out the real context of the situation.
  • THEIR DISTINCTIONS – listening for the distinctions within which they currently see their world and then help them develop new distinctions for creating their world.

Element #3: 10X

In a world where most people are focused on growing 10% bigger, it’s fascinating to help clients put their attention on growing 10 times bigger…

  • IMPOSSIBLE GOALS – expand their thinking and helping them dream big, to create what currently looks impossible.
  • CHALLENGE – challenging and stretching your clients to the very edges of their comfort zone (and beyond!)
  • GOING BEYOND – bringing up uncomfortable topics that will really help them grow.
  • RECOVERY – slow downing top performers to help them balance challenge with recovery.
  • FUN – using humor and fun, plus a willingness to make mistakes and to look silly!

Element #4: LEADERSHIP

This is about you knowing when to lead – and when to hold back. The more successful, intelligent, wealthy or well-known your client, the more they actually crave someone who is willing to challenge their thinking…  

  • SERVE vs PLEASE – serving your clients by leading, getting uncomfortable, or asking the hard questions that are needed.
  • TRUTH TELLING – hiding nothing and holding nothing back, speaking your truth and drawing out theirs, in order to uncover what’s really going on.
  • “I BELIEVE IN YOU” – championing your clients, by celebrating their successes and their failures!
  • THE POWER OF VULNERABILITY – your lack of need need to look good, by sharing your biases, your limits, your weaknesses and your struggles.
  • A 200% RELATIONSHIP – showing up 100% and requiring your clients to show up 100%, too. Taking full responsibility for how you are heard, not just what you say.

Element #5: STRATEGY

Too often coaches jump into Strategy and Problem Solving too quickly. There’s nothing wrong with either but these 5 factors help your clients focus on the what makes the biggest difference…    

  • STRATEGY vs TACTICS – helping your clients develop a personalized strategy and plan of action, rather than something that is cookie cutter.
  • ENVIRONMENT – designing environments for your clients that support their growth.
  • FRONT-LOADING – helping your clients put more effort at the start so they need less self-discipline later.
  • LEARNING – constant learning yourself and recommend experts, books, tools, etc. to help your clients learn and grow.
  • LESS BUT BETTER – help your clients determine what matters most, then make the execution of those things almost effortless.

Oh, and in the tradition of all great magical stories, there’s a secret 6th Element!!

What is it?

Why, it’s yours, of course!

Let me know – what’s your secret sauce? How would you break down the magical element that makes your coaching so special?

Love. Rich

P.S. Whenever you’re ready… here are 4 ways we can help you increase your income and your impact:

  1. If you are ready to play a bigger game with me as your coach and a community of other elite top performers – apply to join us in 4PC. There are now just 5 spots left for January entry. Click here
  2. If you’d like to be coached by me for 3 days straight with 9 fascinating people in a beautiful location, join me on a Deep Dive in London, Los Angeles or Toronto. Click Here.
  3. If you’d like to master The Prosperous Coach Approach, apply for a spot in the November or February Salon. The Nov Salon starts in just a couple of weeks. Click Here.
  4. And if you’ve read The Prosperous Coach and are ready to create your next client, join us in San Diego in April. Click Here.
Transforming world-class leaders into world-class coaches.
That’s what we do.

If this sounds like you, let’s talk and explore if working together is a good fit.

Learn more about ways to work together